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Winter Park Homes For Sale & Real Estate - 274 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 100 S INTERLACHEN AVENUE UNIT 102, WINTER PARK, FL 32789

    $459,00063 Days on yellowkey   MLS ID: O5868332

    30 Days Off yellowkey (back on 7/29/2020)

    For Sale O5868332 - 100 S INTERLACHEN AVENUE UNIT 102, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1267
       Built: 1971   Tax: $2,306 (2019)
    Community: Cloisters Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $2,707 (change assumption)
    Mortgage ($2,515) + Taxes in 2019 ($192)

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    Taxes:$2,306

    Elementary School: Audubon Park K-8

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Audubon Park K-8


  • 1344 PIRATE LANE, WINTER PARK, FL 32792

    $365,00058 Days on yellowkey   MLS ID: O5870205

    19 Days Off yellowkey (back on 7/29/2020)

    REDUCED by $10,000 (2.7%) on 06/29/2020

    For Sale O5870205 - 1344 PIRATE LANE, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1836
       Built: 1983   Tax: $1,627 (2019)
    Community: Harbour Ridge
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,136 (change assumption)
    Mortgage ($2,000) + Taxes in 2019 ($136)

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    Taxes:$1,627

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1631 MEADOWGOLD COURT, WINTER PARK, FL 32792

    $305,00033 Days on yellowkey   MLS ID: O5874375

    19 Days Off yellowkey (back on 7/29/2020)

    For Sale O5874375 - 1631 MEADOWGOLD COURT, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1527
       Built: 1989
    Monthly Fee: $39
       Tax: $2,531 (2019)
    Community: Autumn Glen Ph 3
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,921 (change assumption)
    Mortgage ($1,671) + Fees ($39) + Taxes in 2019 ($211)

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    Taxes:$2,531

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1938 WOODCREST Drive, WINTER PARK, FL 32792

    $275,000197 Days on yellowkey   MLS ID: O5838318

    7 Days Off yellowkey (back on 7/29/2020)

    REDUCED by $24,900 (8.3%) on 03/19/2020

    For Sale O5838318 - 1938 WOODCREST Drive, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1812
       Built: 1981
    Monthly Fee: $100
       Tax: $1,565 (2019)
    Community: Woodcrest
    Pool: No

    Townhouse


    Estimated Monthly Payment: $1,737 (change assumption)
    Mortgage ($1,507) + Fees ($100) + Taxes in 2019 ($130)

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    Taxes:$1,565

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 200 SAINT ANDREWS BOULEVARD UNIT 313, WINTER PARK, FL 32792

    $145,00064 Days on yellowkey   MLS ID: O5868252

    33 Days Off yellowkey (back on 7/29/2020)

    For Sale O5868252 - 200 SAINT ANDREWS BOULEVARD UNIT 313, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 727
       Built: 1970   Tax: $276 (2019)
    Community: Four Seasons
    Pool: No

    Condo


    Estimated Monthly Payment: $818 (change assumption)
    Mortgage ($795) + Taxes in 2019 ($23)

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    Taxes:$276

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1367 CANTERBURY ROAD, WINTER PARK, FL 32789

    $799,90061 Days on yellowkey   MLS ID: O5869015

    0 Days Off yellowkey (back on 7/23/2020)

    REDUCED by $100 (0.0%) on 07/26/2020

    For Sale O5869015 - 1367 CANTERBURY ROAD, WINTER PARK, FL 32789 40 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 3386
       Built: 1945   Tax: $4,524 (2019)
    Community: Orwin Manor Westminster Sec
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,760 (change assumption)
    Mortgage ($4,383) + Taxes in 2019 ($377)

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    Taxes:$4,524

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2019

    Middle School: College Park Middle


  • 915 RAILROAD AVENUE, WINTER PARK, FL 32789

    $319,50065 Days on yellowkey   MLS ID: O5868093

    REDUCED by $5,500 (1.7%) on 07/25/2020

    For Sale O5868093 - 915 RAILROAD AVENUE, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1172
       Built: 1958   Tax: $445 (2019)
    Community: Magnolia Gardens Sub
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,788 (change assumption)
    Mortgage ($1,751) + Taxes in 2019 ($37)

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    Taxes:$445

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 1652 BERKSHIRE AVENUE, WINTER PARK, FL 32789

    $339,90011 Days on yellowkey   MLS ID: O5880445

    For Sale O5880445 - 1652 BERKSHIRE AVENUE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1498
       Built: 1950   Tax: $1,049 (2019)
    Community: Orwin Manor Westminster Sec
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,950 (change assumption)
    Mortgage ($1,862) + Taxes in 2019 ($87)

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    Taxes:$1,049

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 4888 N MAGNOLIA AVENUE, WINTER PARK, FL 32792

    $209,00027 Days on yellowkey   MLS ID: O5876906

    2 Days Off yellowkey (back on 7/25/2020)

    REDUCED by $10,000 (4.6%) on 07/20/2020

    For Sale O5876906 - 4888 N MAGNOLIA AVENUE, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1391
       Built: 1951   Tax: $1,851 (2018)
    Community: Suburban Homes
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,299 (change assumption)
    Mortgage ($1,145) + Taxes in 2018 ($154)

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    Taxes:$1,851

    Elementary School: None

    High School: None

    Tax Year: 2018

    Middle School: None


  • 1620 BOMI CIRCLE, WINTER PARK, FL 32792

    $380,00040 Days on yellowkey   MLS ID: O5872976

    REDUCED by $2,000 (0.5%) on 07/25/2020

    For Sale O5872976 - 1620 BOMI CIRCLE, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2391
       Built: 1984   Tax: $2,972 (2019)
    Community: Tamarak
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,330 (change assumption)
    Mortgage ($2,082) + Taxes in 2019 ($248)

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    Taxes:$2,972

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 511 LANDER ROAD, WINTER PARK, FL 32792

    $335,00027 Days on yellowkey   MLS ID: O5877133

    REDUCED by $10,000 (2.9%) on 07/25/2020

    For Sale O5877133 - 511 LANDER ROAD, WINTER PARK, FL 32792 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1660
       Built: 1957   Tax: $4,308 (2019)
    Community: Eastgate Sub
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,195 (change assumption)
    Mortgage ($1,836) + Taxes in 2019 ($359)

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    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 7748 FOX KNOLL PLACE, WINTER PARK, FL 32792

    $259,90012 Days on yellowkey   MLS ID: O5880421

    For Sale O5880421 - 7748 FOX KNOLL PLACE, WINTER PARK, FL 32792 6 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1298
       Built: 1988
    Monthly Fee: $19
       Tax: $2,814 (2019)
    Community: Bridgewater
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,678 (change assumption)
    Mortgage ($1,424) + Fees ($19) + Taxes in 2019 ($235)

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    Taxes:$2,814

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1140 WASHINGTON AVENUE UNIT 16-C, WINTER PARK, FL 32789

    $405,00012 Days on yellowkey   MLS ID: O5879199

    For Sale O5879199 - 1140 WASHINGTON AVENUE UNIT 16-C, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2069
       Built: 1981   Tax: $2,395 (2019)
    Community: Quarters At Winter Park Phase 2
    Pool: No

    Condo


    Estimated Monthly Payment: $2,419 (change assumption)
    Mortgage ($2,219) + Taxes in 2019 ($200)

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    Taxes:$2,395

    Elementary School: Audubon Park K-8

    High School: Winter Park High

    Tax Year: 2019

    Middle School: None


  • 731 W SWOOPE AVENUE, WINTER PARK, FL 32789

    $319,00012 Days on yellowkey   MLS ID: O5880175

    For Sale O5880175 - 731 W SWOOPE AVENUE, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 884
       Built: 1949   Tax: $2,875 (2019)
    Community: Carver Town
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,987 (change assumption)
    Mortgage ($1,748) + Taxes in 2019 ($240)

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    Taxes:$2,875

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 1500 GAY ROAD UNIT 25D, WINTER PARK, FL 32789

    $199,90012 Days on yellowkey   MLS ID: O5880150

    For Sale O5880150 - 1500 GAY ROAD UNIT 25D, WINTER PARK, FL 32789 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $2,237 (2019)
    Community: Chateaux Du Lac
    Pool: No

    Condo


    Estimated Monthly Payment: $1,282 (change assumption)
    Mortgage ($1,095) + Taxes in 2019 ($186)

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    Taxes:$2,237

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 1370 TIERRA CIRCLE, WINTER PARK, FL 32792

    $325,00012 Days on yellowkey   MLS ID: O5880279

    For Sale O5880279 - 1370 TIERRA CIRCLE, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1650
       Built: 1968   Tax: $2,927 (2019)
    Community: Casa Aloma
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,025 (change assumption)
    Mortgage ($1,781) + Taxes in 2019 ($244)

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    Taxes:$2,927

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1537 SUGARWOOD CIRCLE, WINTER PARK, FL 32792

    $369,00012 Days on yellowkey   MLS ID: G5031174

    For Sale G5031174 - 1537 SUGARWOOD CIRCLE, WINTER PARK, FL 32792 41 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3116
       Built: 1985
    Monthly Fee: $22
       Tax: $2,737 (2019)
    Community: Amberwood Unit 1
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,272 (change assumption)
    Mortgage ($2,022) + Fees ($22) + Taxes in 2019 ($228)

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    Taxes:$2,737

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 2303 SUN VALLEY CIRCLE UNIT 2303, WINTER PARK, FL 32792

    $188,00012 Days on yellowkey   MLS ID: O5880269

    For Sale O5880269 - 2303 SUN VALLEY CIRCLE UNIT 2303, WINTER PARK, FL 32792 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1374
       Built: 1985   Tax: $1,999 (2019)
    Community: Cedarwood Village 1
    Pool: No

    Condo


    Estimated Monthly Payment: $1,197 (change assumption)
    Mortgage ($1,030) + Taxes in 2019 ($167)

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    Taxes:$1,999

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle


  • 1780 OAKHURST AVENUE, WINTER PARK, FL 32789

    $1,190,00041 Days on yellowkey   MLS ID: O5873721

    REDUCED by $109,999 (8.5%) on 07/24/2020

    For Sale O5873721 - 1780 OAKHURST AVENUE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2925
       Built: 2016   Tax: $10,835 (2019)
    Community: Jenkins 2Nd Add
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $7,423 (change assumption)
    Mortgage ($6,520) + Taxes in 2019 ($903)

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    Taxes:$10,835

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Maitland Middle


  • 2495 TAHOE CIRCLE, WINTER PARK, FL 32792

    $189,90055 Days on yellowkey   MLS ID: O5870410

    REDUCED by $6,100 (3.1%) on 07/24/2020

    For Sale O5870410 - 2495 TAHOE CIRCLE, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1981
    Monthly Fee: $312
       Tax: $1,940 (2019)
    Community: Cedarwood Village No 1
    Pool: No

    Condo


    Estimated Monthly Payment: $1,514 (change assumption)
    Mortgage ($1,041) + Fees ($312) + Taxes in 2019 ($162)

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    Taxes:$1,940

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2019

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, South Broward Board of REALTORS®, MIAMI MLS, JTHS MLS, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2020 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.